


Sinful Skirts

by witheringWriter



Series: The Town of Sin [1]
Category: Homestuck
Genre: Alternate Universe - Western, Anal Sex, Crossdressing, Desk Sex, M/M, Oral Sex, Sexual Content
Language: English
Status: Completed
Published: 2014-01-08
Updated: 2014-01-08
Packaged: 2018-01-08 00:25:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,769
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1126171
Author URL: https://archiveofourown.org/users/witheringWriter/pseuds/witheringWriter
Summary: <blockquote class="userstuff">
              <p>The sun in the desert wasn't the only hot thing around and a corset wasn't the tightest thing to get into.</p>
            </blockquote>





	Sinful Skirts

You are the new sheriff in town.

Oh, you wanted a name?

Jake English is what you also go by.

And you think that the heat is absolutely unbearable. It was sweltering hot and you are two minutes away from sweating out blood.

Taking refuge in the local tavern, you took off your hat, fanning yourself with its wide brim. You shifted uncomfortably on the wall you were leaning on, a few frames of things you didn't bother checking moving beneath you. You decided to inspect the area, both out of boredom and also to find a seat somewhere.

The tavern was dimly lit and you couldn't breathe in a single gulp of air without it being properly filtered by smoke. It was reasonably packed, other people trying to escape the glare of the sun, and the sound of music and loud chatter resonated in the small space. You could hear shrill cries and giggles from above you and could see the corridors of the second floor through the banisters. It didn't take you long to realize what was going on up there.

And also what type of place this was.

When you came the the area with the proper training and enthusiasm for the job, the people took you in gladly, mostly because you were such a pushover. Not that you really meant to be. They paid you well and gave you many a (legal, you would tell yourself) favor and in return they followed a few basic rules you set out for them.

However, you made no rules about secret prostitution rings in local taverns.

Also, considering how casually people took it and the fact there were not riots outside the door, you also assumed that this had been going for quite a while.

As much as you didn't want to admit it to yourself, you knew at the back of your head that you were a crooked keeper of justice in the middle of a town of sin. On one hand, you got many gifts for your silence. On the other, it was immoral and downright wrong.

All thoughts of your inability to control the people you govern with you justice were thrown away when you spotted an empty stool by the bar and quickly stepped to take it just before a lady strode over to attempt to take it. You didn't notice until she had her hands on her hips and was tutting at you.

"Oh, I'm sorry Miss-," you paused as you looked up at her. Your brow quirked at the sight of her eyes. Amber. And with your height significantly lower thanks to your sitting position, your eyesight level was straight at her bosom. Or lack of. It made your brow furrow deeper as it was obvious she had some figure. But perhaps it was just the corset, you decided to think.

Your train of thought about the woman was halted by the bartender, another woman who was black. And you meant that as inoffensively as possible. Your tan was a bit light brown by your forearms and face, but this woman was very dark and you would be surprised if you hadn't seen many like her around. Her boldness did come across as the odd thing about her though.

"That ain't no Miss, Sheriff," she sneered. The lady (implied taken? You didn't know) simply rolled her eyes and glared, nose scrunching in the most unladylike way you've seen.

"Must you, Meenah? Honestly, you expect me to pay for board and let you don't let a person go about their civil duty," she said. The lowness of her voice caught you off guard. You assumed she was a smoker and her voice had grown hoarse over the years of use, but it was incredibly low and actually a bit interesting, to put it gently.

"While your pretty face may get ya somewhere, kid, it's only because they don't know the little secret behind the folds of that skirt of yours," she said, laughing loudly after saying her piece.

"Just because I can manage to have something in my skirt, dear," she replied smoothly, and the obvious implication made you red around the collar. You've never heard something so vile from a lady and you could feel the beginning of curious arousal form in your belly, shame nowhere near your mind.

She turned to you, darkened lashes fluttering gently as the black lady scoffed and turned away. You noted how her pale hair was a short bob which was an unusual style for women to have, but probably a smart choice considering how hot it was in your area. Some of her hair was slick, maybe with sweat, and framed her face with a fringe being swept to the her left. As quaint as the do was, it did look like she attempted to cut it with a pocketknife herself.

"I don't suppose you can lend a tired whore a seat?" she said, her low voice piecing you again. You blink, shaking your head of your string of thoughts and cough.

"I apologize. Would you like me to move, Miss?" you ask her, preparing to get up. She shook her head, smiling gently. Or mischievously. You of all people wouldn't be able to tell the difference.

"No, you don't have to. But perhaps I can sit in your lap instead..." She stepped closer, the implication trailing off as she led a had up your thigh very gently. You bet she could feel the pathetic shudder go through your body and you gulped, most likely quite audibly, even through the loud music in the background.

"I don't think that's advisable, Miss," you said. She shook her head.

"Nonsense. There's hardly any room and you did take my seat," she said with a wink. Your blush would probably be noticeable if it weren't for the dim lighting and the tan of your skin, and you let her clamber on you with her low giggle, 

She made herself comfortable in your lap and you could feel the warmth of her thighs and the curve of her buttocks through your pants. You awkwardly put her hand on the side furthest from you to keep her steady and she smiled at you.

She raised her arm and waved it about, calling for the female barkeep, Meenah. Her sleeveless dress exposed parts of a woman you never seen back in your own hometown. Her freckled shoulders were seen and when she raised her arm you could see how her shoulder blade moved and how her skin was virtually smooth and clean, save for the pale hair and scars by her underarm. Probably from trying to cut the hair with a knife, you thought with a frown.

"Get me and the Sheriff something nice, please," you heard the woman ask and saw her pout at the black woman. She scrunched her nose and rolled her eyes.

"Yeah, sure, sure. Lemme get somethin' cool for you two. Since it's our sheriff and all," she said, chuckling as she bent down under the bench to collect two bottles. You didn't mean to peek but you noticed the woman didn't even wear a skirt. She wore the bodice which made you assume she also wore a dress but instead she wore male pants. It made you slightly uncomfortable but you also had to admire her for doing something so bold.

"Thank you kindly," the amber-eyed woman said as she took the bottles from the woman.

"Comin' outta yer pay, dammit," she grumbled a reply as she went back to work, leaning back to watch the woman sing on the makeshift stage at the back of the tavern.

The blonde woman in your lap handed a bottle to you while taking her own. When she undid the stopper of the blasted thing you could notice her muscles tense and the creases it made in her skin when she opened it. You were surprised to realize that even through her male presentation you were fascinated by her even more.

"Did you need help with that?" she asked, nudging your bottle with her own. You shake your head quickly.

"N-no, I'm fine, thank you," you stutter out with a brief chuckle after, biting on the stopper and twisting before pulling it and spitting it out on the ground with the slightest grimace. You had to admit that you were doing it to be a bit of a showoff. The amused smirk you got out of your actions seemed to confirm that she was either impressed or knew exactly what you were doing. But to make yourself feel better you went for both.

"To the heat of the sun," she said, shifting in your lap to raise her bottle to you.

"To the cool of the moon," you replied, a bit bitter about the temperature you already had to deal with. She gave a small laugh and tapped your bottles together, tilting the neck of the bottle and taking a large swig of the drink. 

You watched her drink it in slight awe, seeing her neck move under the little frilled collar she had on with each gulp she took. Some over her beverage trickled down her neck or dripped from her mouth to her chest and you wet your lips unconsciously, eyes darting from her mouth to her flat chest and back again.

Hesitantly, you started to drink from your own bottle, still watching the woman. You could almost feel your hand go slack and your thighs tense when she tilted the bottle back down and licked around the rim of its top, licking up and down the neck to catch whatever drops of bitter honey-colored alcohol she could get. You watched her eyes flutter as she gave an appreciative hum and your mouth hung open slightly, drink forgotten as everything went in slow motion for you.

She looked back at you, her mouth curling deviously and you swear that there was a special place in hell and she was going to be the one to welcome you there.

"See something you fancy, Mister Sheriff?" she teased. You gulped and pushed her off your lap, ignoring her yelp of protest, and made sure she was at least standing when you took a final swig of your drink.

"Thank you for your hospitality, Miss, but I should really go," you quickly blurted, dashing out of the tavern into the scorching heat of the sun.

As you hurried to your station, you sunk into your chair and sighed deeply. You raised your hand to your face and groaned into it, wishing away and praying to God that the boner you had would shoot itself.

-

It was late, probably ten in the evening, and your feet were propped up on your desk and a book was covering your face. You were reading the bible before you dozed off, hoping the pages would give you comfort through your hard time. Figuratively and literally speaking.

The book slid off and shut on the floor loudly, alerting you and making you draw your pistol at the door.

Where she was standing.

"Oh, it's you," you said lamely. You put your gun in your holster after moving a bit of metal behind the trigger you installed as a safety for the weapon after almost shooting your own grandmother. But all thoughts of your granny couldn't stop the thoughts of the woman in front of you flooding.

Well, "woman".

A bit of research in the town files you had in the spare room of your department was done and finally you understood everything that occurred at the bar.

Why the black lady laughed at your formality, why your amber-eyed beauty had a deep voice with its attractive drawl, and why she was flat and muscular, albeit a bit short and stunted,

She was no she at all.

Granted, you were fine if she continued using she if she wished it. You would use it too. But all records indicated otherwise. That even- That even he called himself such.  
"Yes. Me," she-- no, he --replied, a bit amused. He was still wearing the dress and still wore hints of rouge on his face.

"Others said that you were named Dirk," you decided to lie. It was a small half lie. You did get confirmation from others that he was in fact named Dirk but your research indicated that beforehand. "Is this correct?"

"Mhm, my real name, yes," he hummed, walking around your desk to seat herself on it in front of you. His skirt was pulled above the knee so she could cross them, one over the other, to lean on one arm with his hip jutted out. It actually made him look all the more enticing. Despite finding out about the whore, "Desiree"'s little secret, you found yourself to be still as attracted to him as you did when you first met those few hours ago.

"Am I to call you that or would you wish for me to use your-," you paused trying to find an appropriate word before continuing, "your stage name?"

"You mean my whore name, right?" he said with a smirk. You flushed and nodded, unsure if it was alright to. Judging by his laugh, you thought it was fine. "I'd hardly mind what you called me, but if you're asking then it would please me if you used my real name while were alone like this."

The sultry stare he gave you as he said those final words didn't help you and you shifted uncomfortably in your seat. You could see the pink of his tongue dart out to lick his lips and you licked your own, mirroring his action subconsciously. And every fraction of an inch that he drew closer to you, you found yourself moving, leaning up to meet him half way.

"I-Is there a reason why you're here, Dirk?" you mutter, so close to his lips you can taste the essence of his skin. His eyelashes flutter gently and your eyes meet as before he glance down at your lips.

"You know what I want, Sheriff. Lock me up after for being a sinful harlot, but I'd at least like to fulfill my end of your obvious arousal first..." he trailed off. His fingers lightly skimmed the front of your pants and you shudder, rocking into the soft touch. He chuckled gently, uncrossing his legs and grabbing your chair by its arms and dragging you to him.  
But he didn't need to tell you because you leaped up from your chair and crashed your lips together.

Dirk led the messy kiss so that it was was least synchronized and proper instead of the needy heat that you were going to be playing on.

While he was seated on the edge of your desk, you towered over him, pinning him to your table bye his waist. His hands tangled in your hair and he gasped out a moan when your tongue slid against his. The soft flesh of the appendage made you groan and grind down into him and he whined, bucking into you. 

He moved down the table, ankles locking behind your back so he could easily use it to pull himself against your body and rock into your quickly hardening cock. The way his body twisted and how he gasped out your occupation was so lewd and exciting and with your windows open during the night for the cool air and the station open to the public, it made you even more aroused about the possibility of getting caught in such a compromising position.

You moved to latch onto his neck next, mouth working the freckled skin to produce more dark red marks against his tan. He mewled and you'd be lying if you weren't giddy over every sound he made. It made it more arousing when you could feel his erection pressing against your own through his skirt.

Bunching up the fabric, you swiftly tore it away with a hard jerk of your hand and he gasped, quickly being silenced with a hard kiss.

"Ha- E-excited- hah- are you, kitten?" he breathed, back arching as you nipped under his jaw and ripped the frilly collar away with your teeth.

"Y-you seem to have- d-damn- made me this way, chap," you replied with a breathy chuckle, groaning sharply as he undid your belt and made his fingers wrap around your length tightly. He slowly pumped it, licking his lips in that enticing way of his, and pressing the pad of his thumb against head of your cock.

Unlccking his legs from behind you, he got up to kneel on the desk. He leaned over to to your dick pulled it out of your pants to give it and light suck at the tip. You had never experienced such a thing before and your knees almost gave way but his hands firmly gripped at your hips to keep your steady and he swallowed your cock down fluidly in one go. The moan he gave when you were in his mouth vibrated along your length and you gave a loud groan of appreciation, one hand over his and the other raking through his hair.

"O-oh gooood, keep goin' love. Jesus, that is amazing." you grit out, rocking slowly into his mouth and feeling the firm pull of his lips around your dick drag across your shaft. Profanity isn't new to you but it felt so sinfully right to say such things at that moment.

You could feel his tongue flick at the vein on the underside of your cock and you would definitely collapse then if it weren't for the sheer willpower you had to remain upright and more thoroughly enjoy the service being given to you.

You peeked through previously tightly shut eyes to watch Dirk work at your length with his mouth, also noticing him moving his hand along his own length that was weeping pathetically, dribbling precum onto your table. It made you moan, your throat getting caught up as you let your head roll back and your grip in Dirk's hair tighten slightly.

If it wasn't obvious before, you made it obvious then that you wanted so badly to fuck the skirted man by whimpering through your bitten lip how much you wanted to be in him. The small beg was the payment for a very needy moan against your cock before the moaner relinquished your length from his mouth and turned over to brace himself against the desk. It was from this vantage point that you could properly see the tips of two of his fingers working the entrance of his ass under his feminine undergarments and it made you nervous and needy all at the same time.

"Hurry up. I've waited all day for this," he said in a harsh whisper.

Again, you didn't need to be told twice because you quickly removed his hand, ripped away his underwear, and sheathed your dick inside of him so you could fuck him roughly into your table.

His first cry of protest dissolved quickly into needy pants, directing his ass against your front to find his own pleasure while you found your own in the tightness and heat of his whore hole.

"Oh- oh fuck- Dirk--!!" You gripped his hips tightly, slamming into him and relishing the feel of his ass clamping on you under his skirt. He nodded, crying out his moans and scratching at the wood beneath him as he mewled, working himself while you fucked him.

"Sh-Sheriff, I'm-- I'm gunna explode-- s-so good--!" he cried wantonly. And god fuck, that whore could sing for you. The way his voice broke from the its lowness to a pathetic high-pitched whine made you slam into him faster, feeling your legs about to give in as they tensed as you drew close to your edge.

"A-Almost there, love--," you gasped out, your blunt nails digging into his hips. He nodded and looked at you over his shoulder. Your brows furrowed, sweat glistening from your forehead, and you felt the muscles of Dirk's ass tense, alerting you of his closeness as well.

Finding a reason to continue without giving up to your own need for release, you searched for the spot he moved his ass towards, assuming that like women he had his own spot. His yelp and the way he moaned "oh god there" gave you every indication that there was where you were to aim. 

You were aware you didn't hit that spot every time but the times you did you enjoyed the delicious tightness that came with hitting it perfectly. 

It was eventually with a sharp gasp that you could feel the final tightness before the sound of a gasp of relief that you took as Dirk being spent. However, you were not done. So before the last of his tightness dissipated into a sated relaxed state, your rammed into him before emptying the load you kept from releasing inside him, hearing him hiss gently when you had finished.

You pulled out slowly, seeing Dirk wince. You patted his head gently and did the only thing you thought would be appropriate.

You kissed his forehead. 

You didn't miss the slight look of surprise he had before rubbing your eyes and licking your chapped lips, sinking back into your chair again. 

Dirk slid off the desk, wobbling as he stood, and pulled his skirt down. You watched the sight of his freckled buttocks and your spunk sliding down his thigh disappear from you view and then continued to watch as he attempted to toe his bloomers despite already wearing his heeled boots.

He shakily walked back to you, tucking your flaccid cock back into your pants and doing your belt back up. He straddled your waist with a small wince as his thighs were separated again and wrapped his arms around your neck.

"I take it you enjoyed yourself," he said a bit hoarsely. From his loud moaning you could only feel sympathetic at how horrible his voice sounded. But the pity was long gone and replaced by pride since you made him sound so horrid.

"Thoroughly," you replied, rubbing his sides gently. He hummed gently and his eyes fluttered shut as he leaned his forehead against yours.

"We should do this again sometime," he said, smiling tiredly and allowing a small chuckle escape his lips.

You nodded and gave your own smile, gently pressing your lips to the corner of his mouth as he continued to smile lazily at you.

"Definitely."

**Author's Note:**

> my mom is making me watch shitty western movies and i hate it ew


End file.
